N-Bromosuccinimide (NBS) is an organic compound commonly used as a brominating agent in organic synthesis. It is a convenient source of bromine radicals. It is used in radical bromination of allylic and benzylic positions. Additionally, NBS is also used as a reagent in electrophilic addition and electrophilic substitution reactions in organic chemistry.
N-Bromosuccinimide can be used as a reagent:
- In the Wohl-Ziegler reaction (bromination at allylic positions via a radical pathway).
- To synthesize benzils and aliphatic 1,2-diketones from hydrobenzoins and 1,2-diols in the presence of CCl4 as a solvent.
- To prepare tricyclic azepino[4,5-b]indoles from indole-β-enaminoesters or β-enaminones via Pictet–Spengler cyclization.
- To synthesize acylsilanes via oxidative hydrolysis of 2-silyl-1,3-dithianes.
Versatile brominating agent. For the oxidation of tryptophan though tyrosine, histidine and methionine residues may be oxidized to a lesser extent. Also used for the modification of ribosomal sulfhydryl groups.
5 g in glass bottle
100, 250, 500 g in poly bottle
1, 5 kg in poly bottle
Features and Benefits
NBS is an easier and safer brominating agent to handle than bromine.
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC